Atropisomerism in the vaptan class of vasopressin receptor ligands: The active conformation recognized by the receptor

Hidetsugu Tabata; Jun Nakagomi; Daisuke Morizono; Tetsuta Oshitari; Hideyo Takahashi; Hideaki Natsugari

doi:10.1002/anie.201007772

Atropisomerism in the vaptan class of vasopressin receptor ligands: The active conformation recognized by the receptor

Hidetsugu Tabata
, Jun Nakagomi
, Daisuke Morizono
, Tetsuta Oshitari
, Hideyo Takahashi
, Hideaki Natsugari

Faculty of Pharmaceutical Sciences

Teikyo University
Institute of Science Tokyo

Research output: Contribution to journal › Article › peer-review

55 Scopus citations

Abstract

(Chemical Equation Presented) Latent chirality: Atropisomerism in the vaptan class of vasopressin receptor ligands with N-benzoyl benzo-fused seven-membered-ring nitrogen heterocycles was investigated by freezing the axis by ortho substitution. The aS/aR atropisomers caused by the Ar-N(=CO) axis were separated to reveal that the vasopressin receptor recognizes the cis,aS conformation (see picture; R=CH₃, X= -CO-, Y=H) when it binds to the ligand.

Original language	English
Pages (from-to)	3075-3079
Number of pages	5
Journal	Angewandte Chemie - International Edition
Volume	50
Issue number	13
DOIs	https://doi.org/10.1002/anie.201007772
State	Published - 21 Mar 2011

Keywords

1,5-Benzodiazepine
Atropisomerism
Chirality
Receptors
Vasopressin

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10.1002/anie.201007772

Cite this

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title = "Atropisomerism in the vaptan class of vasopressin receptor ligands: The active conformation recognized by the receptor",

abstract = "(Chemical Equation Presented) Latent chirality: Atropisomerism in the vaptan class of vasopressin receptor ligands with N-benzoyl benzo-fused seven-membered-ring nitrogen heterocycles was investigated by freezing the axis by ortho substitution. The aS/aR atropisomers caused by the Ar-N(=CO) axis were separated to reveal that the vasopressin receptor recognizes the cis,aS conformation (see picture; R=CH3, X= -CO-, Y=H) when it binds to the ligand.",

keywords = "1,5-Benzodiazepine, Atropisomerism, Chirality, Receptors, Vasopressin",

author = "Hidetsugu Tabata and Jun Nakagomi and Daisuke Morizono and Tetsuta Oshitari and Hideyo Takahashi and Hideaki Natsugari",

year = "2011",

month = mar,

day = "21",

doi = "10.1002/anie.201007772",

language = "英語",

volume = "50",

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journal = "Angewandte Chemie - International Edition",

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T1 - Atropisomerism in the vaptan class of vasopressin receptor ligands

T2 - The active conformation recognized by the receptor

AU - Tabata, Hidetsugu

AU - Nakagomi, Jun

AU - Morizono, Daisuke

AU - Oshitari, Tetsuta

AU - Takahashi, Hideyo

AU - Natsugari, Hideaki

PY - 2011/3/21

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N2 - (Chemical Equation Presented) Latent chirality: Atropisomerism in the vaptan class of vasopressin receptor ligands with N-benzoyl benzo-fused seven-membered-ring nitrogen heterocycles was investigated by freezing the axis by ortho substitution. The aS/aR atropisomers caused by the Ar-N(=CO) axis were separated to reveal that the vasopressin receptor recognizes the cis,aS conformation (see picture; R=CH3, X= -CO-, Y=H) when it binds to the ligand.

AB - (Chemical Equation Presented) Latent chirality: Atropisomerism in the vaptan class of vasopressin receptor ligands with N-benzoyl benzo-fused seven-membered-ring nitrogen heterocycles was investigated by freezing the axis by ortho substitution. The aS/aR atropisomers caused by the Ar-N(=CO) axis were separated to reveal that the vasopressin receptor recognizes the cis,aS conformation (see picture; R=CH3, X= -CO-, Y=H) when it binds to the ligand.

KW - 1,5-Benzodiazepine

KW - Atropisomerism

KW - Chirality

KW - Receptors

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DO - 10.1002/anie.201007772

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AN - SCOPUS:79952666391

SN - 1433-7851

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JO - Angewandte Chemie - International Edition

JF - Angewandte Chemie - International Edition

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Atropisomerism in the vaptan class of vasopressin receptor ligands: The active conformation recognized by the receptor

Abstract

Keywords

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CCDC 803350: Experimental Crystal Structure Determination

CCDC 803349: Experimental Crystal Structure Determination

CCDC 803351: Experimental Crystal Structure Determination

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Atropisomerism in the vaptan class of vasopressin receptor ligands: The active conformation recognized by the receptor

Abstract

Keywords

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Datasets

CCDC 803350: Experimental Crystal Structure Determination

CCDC 803349: Experimental Crystal Structure Determination

CCDC 803351: Experimental Crystal Structure Determination

Cite this